Send to

Choose Destination
See comment in PubMed Commons below
J Am Chem Soc. 2005 Dec 28;127(51):18006-7.

Air-assisted addition of grignard reagents to olefins. A simple protocol for a three-component coupling process yielding alcohols.

Author information

Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Yokohama, Kanagawa 226-8501, Japan.


Silylmethyl, tertiary-alkyl, alkenyl, and aryl Grignard reagents underwent intermolecular addition to olefins, such as styrenes, conjugated dienes, and enynes under an air atmosphere to give homologated alcohols. For example, (trimethylsilyl)methylmagnesium chloride and alpha-methylstyrene in ether at room temperature under dry air directly furnished 2-phenyl-4-(trimethylsilyl)-2-butanol in good yield. As the Grignard addition to olefins under argon with rigorous exclusion of O2 did not proceed at all, the above reaction should involve a radical mechanism: an alkyl radical generated by the aerial oxidation of the Grignard reagent adds to olefin, which is followed by oxygenation. Representative examples of this transformation, where products were obtained in good to excellent diastereo- or regioselectivity, are also disclosed.

PubMed Commons home

PubMed Commons

How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society
    Loading ...
    Support Center